Water → HCID 22163834, compound

HRID 1087778Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][C:30](=[O:54])[CH2:31][CH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34](=[O:41])[N:33]1[C:42]1[CH:51]=[CH:50][C:49]2[C:44](=[N:45][C:46]([O:52][CH3:53])=[CH:47][CH:48]=2)[N:43]=1)(C(C)(C)C)(C)C.O>O1CCCC1>[OH:26][CH2:27][CH2:28][CH2:29][C:30](=[O:54])[CH2:31][CH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34](=[O:41])[N:33]1[C:42]1[CH:51]=[CH:50][C:49]2[C:44](=[N:45][C:46]([O:52][CH3:53])=[CH:47][CH:48]=2)[N:43]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Tetrabutylammonium fluoride (11.5 g) is added in small portions at a temperature in the region of 0° C. to a solution of 3-(5-tert-butyldimethylsilyloxy-2-oxopentyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (9.2 g) in anhydrous tetrahydrofuran (185 cc), and the solution obtained is stirred for 5 minutes at a temperature in the region of 0° C. The reaction mixture is then stirred for 1 hour 30 minutes at a temperature in the region of 20° C. and then poured into a mixture of ice (200 g) and water (600 cc). The insoluble product is separated by filtration, washed successively with water (5×25 cc) and diisopropyl ether (2×10 cc) and dried in the air. After recrystallization in acetonitrile, 3-(5-hydroxy-2-oxopentyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (5.6 g), m.p. 152° C., is obtained.

Workup

customthe solution obtained
stirringThe reaction mixture is then stirred for 1 hour 30 minutes at a temperature in the region of 20° C.
customThe insoluble product is separated by filtration
washwashed successively with water (5×25 cc) and diisopropyl ether (2×10 cc)
customdried in the air
customAfter recrystallization in acetonitrile

Sources & evidence

ORD record: ord-1ef6732fe3cf4d34a6e5793ba528fbb5
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960779

Reaction notes

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